HomeAway is the world leader in vacation rentals with over 1 million listings. We offer the largest selection of properties for any travel occasion and every budget. We're committed to helping families and friends find a perfect vacation rental to create unforgettable travel experiences together.

Vacation Rentals in Big Pine Key: Houses, Condos & More

This single family home has been totally renovated with new everything. Tiled floors throughout, large granite counter top, stainless steal appliances, decorative lighting, modern bathrooms, and a large wrap around balcony with comfortable patio f...

A huge luxury retreat, the perfect combination of high end living and tropical comfort, you’ll be comfortable here in high heels or flip flops!
You’ll wake up in the morning and dine al fresco on our 40 foot screened in lanai/terrace. Perhaps th...

' Sunset Point ', is a stately private home situated at the very end of a point overlooking a beautiful protected lagoon. Sombrero Country Club and golf course are directly across the water nestled behind a shoreline of lush mangroves, providi...

To get a detailed accounting of your rental costs please enter your rental dates in the upper right corner of the site and look for an instant quote. See COMPLETE "rates" section for more detailed information.
'Sunset Point', is a stately priva...

Island View is a charming three bedroom estate situated on three tropical landscaped lots that overlook the Atlantic Ocean and provide you with your own private paradise. Boasting expansive ocean views, and a heated oceanfront pool and tiki bar, ...

Welcome to Betty’s Place on Treasure Cove, where peace and tranquility are the order of the day. Conveniently located off U.S. Hwy 1, with local grocery, pharmacy and discount department stores only 2 miles up the road, and within walking distance...

Vacation Rentals in Big Pine Key: Houses, Condos & More

This single family home has been totally renovated with new everything. Tiled floors throughout, large granite counter top, stainless steal appliances, decorative lighting, modern bathrooms, and a large wrap around balcony with comfortable patio f...

A huge luxury retreat, the perfect combination of high end living and tropical comfort, you’ll be comfortable here in high heels or flip flops!
You’ll wake up in the morning and dine al fresco on our 40 foot screened in lanai/terrace. Perhaps th...

' Sunset Point ', is a stately private home situated at the very end of a point overlooking a beautiful protected lagoon. Sombrero Country Club and golf course are directly across the water nestled behind a shoreline of lush mangroves, providi...

To get a detailed accounting of your rental costs please enter your rental dates in the upper right corner of the site and look for an instant quote. See COMPLETE "rates" section for more detailed information.
'Sunset Point', is a stately priva...

Island View is a charming three bedroom estate situated on three tropical landscaped lots that overlook the Atlantic Ocean and provide you with your own private paradise. Boasting expansive ocean views, and a heated oceanfront pool and tiki bar, ...

Welcome to Betty’s Place on Treasure Cove, where peace and tranquility are the order of the day. Conveniently located off U.S. Hwy 1, with local grocery, pharmacy and discount department stores only 2 miles up the road, and within walking distance...